1,3-Difluoroacetone → (R)-1-(1,3-difluoropropan-2-yl)pyrrolidin-3-amine
Reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6]C(=O)OC(C)(C)C)[CH2:2]1.[F:14][CH2:15][C:16](=O)[CH2:17][F:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:14][CH2:15][CH:16]([N:1]1[CH2:5][CH2:4][C@@H:3]([NH2:6])[CH2:2]1)[CH2:17][F:18]Participants
5
Procedure
To a solution of (R)-tert-butyl pyrrolidin-3-ylcarbamate (0.500 g) and 1,3-difluoropropan-2-one (0.278 g) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (0.853 g). After stirring for 1 hour, the reaction was quenched with saturated NaHCO3 solution (5 mL). The product was extracted into dichloromethane (25 mL), dried over magnesium sulfate, filtered, and concentrated. The resulting crude material was treated with HCl (4.0M in dioxane, 4 mL) and methanol (1 mL) and stirred for 1 hour.
Workup
- customthe reaction was quenched with saturated NaHCO3 solution (5 mL)
- extractionThe product was extracted into dichloromethane (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- additionThe resulting crude material was treated with HCl (4.0M in dioxane, 4 mL) and methanol (1 mL)
- stirringstirred for 1 hour
Sources & evidence
- ORD record
- ord-5f7264f962ce4a219beb6f4f63988c8e
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303025B2
Reaction notes
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